16107-82-7Relevant academic research and scientific papers
Ring-Opening Rearrangements of 2-(Benzotriazol-1-yl) Enamines and a Novel Synthesis of 2,4-Diarylquinazoline
Katritzky, Alan R.,Yang, Baozhen,Jiang, Jinlong,Steel, Peter J.
, p. 246 - 249 (1995)
2-(Benzotriazol-1-yl) enamines (readily available from lithiated 1-(arylmethyl) benzotriazole and nitriles) undergo facile rearrangement into 2,4-diarylquinazolines.A plausible mechanism for this novel rearrangement is proposed and supported.
Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines
Wang, Chao,Rui, Xiyan,Si, Dongjuan,Dai, Rupeng,Zhu, Yueyue,Wen, Hongmei,Li, Wei,Liu, Jian
supporting information, p. 2825 - 2833 (2021/04/26)
The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).
Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines
Wang, Zijuan,Chen, Wenteng,He, Chang,Zhang, Guolin,Yu, Yongping
, p. 1356 - 1364 (2020/11/09)
A one-pot method for joining three separate components leading to an assortment of 4-arylquinazolines (27 examples) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed?-cascade reaction involving C(sp)-C(sp 2/s
TMSOTf-catalyzed synthesis of substituted quinazolines using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
Chan, Chieh-Kai,Lai, Chien-Yu,Wang, Cheng-Chung
, p. 7201 - 7212 (2020/10/02)
In this article, we report an efficient and mild synthetic route for the construction of substituted quinazolines from functionalized 2-aminobenzophenones with various benzaldehydes usingcat. TMSOTf and hexamethyldisilazane (HMDS) under neat, metal-free and microwave irradiation conditions in which gaseous ammonia was formedin situ. This synthetic protocol provided the desired quinazolines with a broad substrate scope in good to excellent yields. Some structures were confirmed by X-ray single-crystal diffraction analysis.
Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines
Zhu, Jianghe,Shao, Yinlin,Hu, Kun,Qi, Linjun,Cheng, Tianxing,Chen, Jiuxi
, p. 8596 - 8603 (2018/11/27)
The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, ha
Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines
Cheung, Wing,Patch, Raymond J.,Player, Mark R.
, p. 2368 - 2371 (2018/05/25)
A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C–H activation/C–N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.
Heterogeneous oxidative synthesis of quinazolines over OMS-2 under ligand-free conditions
Li, Bo,Li, Changming,Tian, Liang,Zhou, Jinbo,Huang, Jianfeng,Meng, Xu
supporting information, p. 15985 - 15989 (2018/10/04)
A manganese oxide octahedral molecular sieve (OMS-2) prepared using urea as an additive was found to be an efficient recyclable catalyst for the synthesis of quinazolines via oxidation/cyclization. A broad range of substituted quinazolines were obtained from alcohols and amidines in good yields under ligand-free conditions. OMS-2 was characterized by XRD, BET, ICP-AES, SEM, TEM and XPS, which indicated that the superior catalytic ability might arise from enhanced surface area and crystallinity.
Palladium-Catalyzed Three-Component Tandem Process: One-Pot Assembly of Quinazolines
Hu, Kun,Zhen, Qianqian,Gong, Julin,Cheng, Tianxing,Qi, Linjun,Shao, Yinlin,Chen, Jiuxi
supporting information, p. 3083 - 3087 (2018/05/28)
The first example of the palladium-catalyzed, three-component tandem reaction of 2-aminobenzonitriles, aldehydes, and arylboronic acids has been developed, providing a new approach for one-pot assembly of diverse quinazolines in moderate to good yields. A noteworthy feature of this method is the tolerance of bromo and iodo groups, which affords versatility for further synthetic manipulations. Preliminary mechanistic experiments indicate that this tandem process involves two possible mechanistic pathways for the formation of quinazolines via catalytic carbopalladation of the cyano group.
Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines
Ye, Xinglin,Yuan, Jianjun,Zhou, Yirong,Deng, Zhihong,Mao, Xuechun,Peng, Yiyuan
, p. 3976 - 3984 (2016/11/11)
An efficient route to 4-substituted quinazolines by arylation or alkylation of quinazolinones under mild conditions is described. 4-Tosyloxyquinazolines were obtained through the reaction of quinazolinones and p-methylbenzenesulfonyl chloride in the presence of K2CO3. The cross-coupling reaction of 4-tosyloxyquinazolines with organoindium reagents, carried out in tetrahydrofuran, catalyzed by Pd2(dba)3/ (2-furyl)3P led to the formation of 4-functionalized quinazolines in good to excellent yields. Higher yields were obtained by the one-pot reaction of quinazolinone, p-methylbenzenesulfonyl chloride, Pd2(dba)3-/(2-furyl)3P, and organoindium reagent. These methods using organoindium compounds as coupling partners provided an efficient route to 4-(hetero)aryl/alkylquinazolines, especially 4-substituted quinazolines bearing a halogen scaffold.
Copper-catalyzed aerobic oxidative decarboxylative amination of arylacetic acids: A facile access to 2-arylquinazolines
Yan, Yizhe,Shi, Miaomiao,Niu, Bin,Meng, Xiangping,Zhu, Changrui,Liu, Gengyao,Chen, Ting,Liu, Yanqi
, p. 36192 - 36197 (2016/05/19)
An efficient copper-catalyzed oxidative decarboxylative amination of arylacetic acids with 2-aminobenzoketones and ammonium acetate under an oxygen atmosphere was first developed. This reaction represents a novel avenue for 2-arylquinazolines in good to e
